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Chemical Structure| 89466-08-0 Chemical Structure| 89466-08-0

Structure of 2-Hydroxyphenylboronic acid
CAS No.: 89466-08-0

Chemical Structure| 89466-08-0

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Product Details of [ 89466-08-0 ]

CAS No. :89466-08-0
Formula : C6H7BO3
M.W : 137.93
SMILES Code : C1=C(C(=CC=C1)B(O)O)O
MDL No. :MFCD01074581
InChI Key :YDMRDHQUQIVWBE-UHFFFAOYSA-N
Pubchem ID :2773454

Safety of [ 89466-08-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501

Computational Chemistry of [ 89466-08-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 3.0
Molar Refractivity 38.29
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

60.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.02
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.93
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.36
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.2
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.29

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.72
Solubility 2.65 mg/ml ; 0.0192 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.88
Solubility 1.8 mg/ml ; 0.0131 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.68
Solubility 28.6 mg/ml ; 0.207 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.42 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.52

Application In Synthesis of [ 89466-08-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 89466-08-0 ]

[ 89466-08-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 5847-59-6 ]
  • [ 89466-08-0 ]
  • [ 96661-32-4 ]
  • 2
  • [ 89466-08-0 ]
  • [ 685892-23-3 ]
  • 7-chloro-6H-benzo[c]chromen-6-one [ No CAS ]
  • 3
  • [ 89466-08-0 ]
  • [ 57381-62-1 ]
  • 9-chloro-6H-benzo[c]chromen-6-one [ No CAS ]
  • 4
  • [ 89466-08-0 ]
  • [ 878207-28-4 ]
  • [ 1238197-06-2 ]
  • 5
  • [ 106-37-6 ]
  • [ 89466-08-0 ]
  • [ 26608-06-0 ]
  • 6
  • [ 13195-50-1 ]
  • [ 89466-08-0 ]
  • 2-(5-nitrothiophen-2-yl)phenol [ No CAS ]
  • 9
  • [ 87611-00-5 ]
  • [ 89466-08-0 ]
  • C14H8ClFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With potassium fluoride; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 20℃; for 1.5h;Inert atmosphere; B-2 (2.17 g, 10.0 mmol) and 2-hydroxybenzene boronic acid (1 .38 g, 10.0 mmol) were dissolved in 10 mL of THF. To the solution was added potassium fluoride (1.74 g, 30.0 mmol) dissolved in 5 mL of water, and the mixture was evacuated and purged with Argon gas. Then, 'Betaupsilon3Rho-EtaBetaRho4 (290 mg, 1.00 mmol) and Pd(OAc)2 (225 mg, 1.00 mmol) were added to the mixture, and the mixture was stirred at room temperature for 1 .5 h. The reaction mixture was dried with MgS04, filtrated over Celite and washed with ethyl acetate. The crude was purified by column chromatography on silica gel eluting with a mixed solvent of heptane and ethyl acetate (3:1 ) to yield 2.27 g (96%) of B-3 as a slightly yellow solid. It was used for next reaction without purification.
  • 10
  • [ 6287-82-7 ]
  • [ 89466-08-0 ]
  • 2-(3-bromobenzo(b)thiophen-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃; for 6h;Schlenk technique; accurately weighed 2,3-dibromobenzo [fo] thiophene (683 mg, 2.34 mmol), 2-light benzene phenylboronic acid (484 mg, 3.5(1 · 29 g, 9.36 mmol), tetrakis (triphenylphosphine) palladium (0.05 equivalent), 1,4-dioxane Hexahedral / water (volume ratio 4: 1), placed in a 90 C oil bath for 6 hours. After completion of the reaction, the solvent was removed under reduced pressure, and silica gel column separation, petroleum ether / ethyl acetate was used as the eluent to give 2- (3-bromobenzothiazol-2-yl) phenol 3a in 84% yield.
  • 11
  • [ 3032-81-3 ]
  • [ 89466-08-0 ]
  • 3′,5′-dichloro-[1,1′-biphenyl]-2-ol [ No CAS ]
  • 12
  • [ 89466-08-0 ]
  • [ 118289-17-1 ]
  • C12H9NO2 [ No CAS ]
 

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